On The Head Of A Pin AU
by SierraKathleen
Summary: Dean Winchester locked alone in a room with his former master, Alastair? Something's bound to go wrong…. terribly, terribly wrong. Rated M for Mature Content.


**Disclaimer: **I own nothing, Supernatural belongs to Eric Kripke and large television corporations such as the CW. Any and all of the following is completely fictional and fan-made.

And of course, most of what is written here is purely the genius of writer Ben Edlund for this season four episode. My thoughts dawdle and interrupt every now and then, but I offer the script credit fully to him.

**Author's Note: **I was in the mood for some Alastair and Dean lovin' but I didn't want to go and make a whole new storyline, so on and so forth. At any rate, here is the result of desires.

**Summary: **Dean Winchester locked alone in a room with his former master, Alastair? Something's bound to go wrong…. terribly, terribly wrong.

**Pairings:** ALASTAIR//DEAN – Don't like, don't read. Simple as that.

Without anything further, please enjoy!!

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**- On The Head Of A Pin -**

(ALTERNATE UNIVERSE)

In some kind of sickening flash, Dean Winchester was transported to an abandoned warehouse with the angels Castiel and Uriel as his only company. _Splendid._ Turning swiftly, Castiel directed Dean to a door which held a tiny window meshed with wire towards the top. Through it he could see Hell's master himself – Alastair. Dean's pulse began to accelerate just at the look of him, terror shredding through him in tiny prickling waves.

"This devil's trap is old Enochian," Castiel explained in his usually rough voice, "He's bound completely."

Dean could feel a tight lump beginning to form in his throat already. Not be able to stand the sight in front of him any longer, he turned from the door muttering in a hushed tone, "Fascinating. Where's the door?"

"Where are you going?" Castiel asked almost instantly, turning to follow Dean like a lost puppy.

_Good pet_, Alastair thought, smirking smugly to himself. Moving a clump of thick saliva to the side of his mouth, Alastair allowed it to spill over the edge of his meatsuit's lips and splatter onto the concrete below. Glancing downward, Alastair had a chance to overlook his host. Sure, he'd considered the pros and cons of his little human costume when he'd selected him, but looks were really the least of his worries. Still, now actually getting a chance to just stand back and examine the flesh, Alastair was pleased – certainly an improvement from his last ensemble. A bit younger, perhaps? All of this meant little to him, however, as he wretched uncomfortably against the damned devil's trap. _Oh dear,_ Alastair sighed to himself, _What could these sanctimonious pricks possibly be doing to keep my favorite pupil from me?_

Almost as if on cue the door busted open, Dean following behind pushing a wheeled cart concealed in a dark cloth. Alastair could see Castiel standing solemnly in the distance with his hands nestled deep into the pockets of his vessel's trench coat, which of course only made his delight grow further. Hearing the dull squeak of the wheels pushing against the floor below, Alastair decided to chime in with his own humility. "Heaven, I'm in heaven," he sang, his voice coming out groggier than he would've liked, "and my heart beats so that I can hardly speak. I seem to find the happiness I seek, when we're out together dancing cheek to cheek."

As he finished with his short performance of lyrics, Alastair thrashed his body towards Dean as if asking him for a dance. This of course made his limbs throb with a dull ache – _damn human confinement_ – but hey, when in Rome right? Still, Dean remained unnervingly silent, which was disappointing to the demon. He longed to here even a rough gasp escape his throat. Lifting a hand, Dean carelessly tossed the tarp from the cart revealing its contents. Alastair snickered at the pitiful instruments displayed before him, this was nothing compared to the wonders which could be found in the bowls of Hell.

Alastair decided now would probably be the best time to break the ice, clearing his throat to find his voice once more. "I'm sorry. This is a very serious, very emotional situation for you," he mocked in false sympathy, "I shouldn't laugh, it's just that – I mean, are they serious? They sent you to torture me?"

Dean turned, taking a few steps closer to the devil's trap so that he and Alastair were only about a foot apart – maybe less. "You got one chance. One. Tell me who's killing the angels. I want a name," Dean murmured, his voice barely grazing a whisper. Still, there was an element of stern authority which Alastair had always respected about Dean.

Even in the gravest of situations, the Winchester had always managed to keep a secure dominance to his voice – that is unless his insides were being carved out with a razor. That was a different story entirely. Alastair wouldn't allow it to be that easy for the kid though, no he had to have _some_ fun with this little private session of theirs. "You think I'll see all your scary toys and spill my guts?" Alastair asked, keeping his eyes focused intently on Dean.

Dean overlooked his old master from head to toe, inhaling somewhat as if taking him in all over again. Dean liked this body – it was odd to admit, but just about anything was better than the horrific sight of the _true_ demon Alastair. There was a certain element though that Dean liked, and so in this moment he thought that perhaps this experience wouldn't be so awfully bad after all. Shrugging almost nonchalantly, he retorted, "Oh, you'll spill your guts, one way or another. I just didn't wanna ruin my shoes."

Alastair could feel a slight grin pulling at the corners of his lips in turn from Dean's response. "Oh, yeah," he purred seductively, reminiscing on all the good times he and Dean shared amidst the flames. When Dean was _off_ the rack, that is.

"Now answer the question," Dean almost growled, inching just slightly towards the demon's face despite his deeply buried desire to bolt out of here as fast as his legs would carry him.

"Or what? You'll work me over?" Alastair asked, arching an eyebrow when Dean's expression softened somewhat, "But then, maybe you don't want to. Maybe you're, ah, scared to."

Dean swallowed hard, now feeling slightly intimidated by the demon before him. That was the one thing he hated most about Alastair, but hated even more about himself – he could so easily torment Dean, get under his skin. It was enough to make the hunter want to crouch down and start pulling out his hair. Still, he kept his cool, as usual, and disguised his discomfort with a semi-smirk. After a long pause, he mused, "I'm here, aren't I?"

Alastair hardly needed to think twice before spatting out his answer. "Not entirely. You left part of yourself back in the _pit_. Let's see if we can get the two of you back together again, shall we?" he urged.

Dean stood in silence for a moment, actually thinking over Alastair's offer. _You left part of yourself back in the pit_, Dean played over the words in his head time and time again. What if that was the truth? After all, there was a hole, a hole so deep it bore right through, carved deep inside the elder Winchester. Shaking that thought quickly from his head however, Dean replied simply, "You're gonna be disappointed." With that, he turned away from his tormentor to face the cart just behind.

"You have not disappointed me so far," Alastair stated proudly, as if praising a small child on a good deed. A moment of silence clung between the two, thickening with some unspoken tension as it continued to linger. "Come on," the demon continued finally, wanting so badly to strike a match somewhere deep inside the furious flames of Dean, "You gotta want a little payback for everything I did to you. For all the _pokes_ and _prods_. Hmm?"

Slipping his leather jacket off his arms, Dean laid it gently aside working quickly to rearrange the tools which lay before him. As his fingers stroked each handle, each blade, chills ran down Dean's spine as he recalled upon the first time he stepped off the rack. Picking up the rounded silver cup nearby, Dean slammed it down firmly now lifting the rather large jug of holy water to its rim. He watched as the pure liquid spilt into the cup, the rosary clanging against the side the entire while. "Now we're getting somewhere," Alastair muttered in a hushed voice, licking his lips delicately, "Holy water? Come _on_. Grasshopper, you're gonna have to get creative to impress me." Alastair chuckled somewhat to himself, picturing Dean as a tiny insect in which he would absolutely love to just pull the wings from. Limit his ability to fly, crush his dreams perhaps?

Just then, Dean paused abruptly from his pouring of the water, stopping to look up at Alastair with a new element swirling in his glowing hazel eyes. Pouting ever slightly, Dean slipped his tongue out to moisten his lips prior to casually stepping over towards the rack once more. When he crossed the border of the carefully drawn symbols, he didn't stop, but still urged forward until at last he was only inches from Alastair's face. Alastair let out a soft breath he didn't realize he'd been holding in while waiting for his former apprentice to make his next move. Dean placed one hand against the frame behind Alastair, leaning his weight on it which caused him to come closer yet. Now they're lips were less than an inch apart, each one's breath steaming against the other's face.

"Oh yeah?" Dean mumbled in a low and gruff voice, "How's this for creative?" Without warning, the hunter drove himself forward connecting his own lips with the demon's – but not in the way you'd expect. Instead, using his pearly whites, Dean bit down on Alastair's lower lip causing an irony red liquid to spill onto Dean's tongue.

Alastair screamed out in sudden and unexpected pain. His whole body shuddered, wriggling in attempts to break free from Dean's vice grip. At last Dean removed his teeth from Alastair's now throbbing flesh. The hunter turned from him just slightly, spitting out a mouthful of Alastair's blood – and possibly some tiny bits of his inner lip. "There's plenty more where that came from," Dean muttered, clearing his throat.

Alastair waited a moment for the bleeding to temporarily subside, allowing himself to spit out some scarlet. "Go. Directly. To. Hell," he growled miserably, "Do not pass go, do not collect two hundred dollars."

Dean smiled openly at the demon's statement – he was getting somewhere now. _Peachy_. "Those are pretty tough words," he mused, "considering _you're_ the one strapped to the rack this time." Meanwhile, Dean turned back to the wooden cart, continuing his business with the holy water.

Alastair cocked his head to the side, watching as Dean coated Ruby's infamous blade in the heavenly liquid. "Do you really think this is gonna fix you?" he asked, looking over Dean's rugged body language, "Give you closure? That is sad. That's really sad. Sad, sad."

Taking some leisurely steps forward once more, Dean ignored Alastair's stalling words, approaching the rack once more. He held the knife close to the demon's face, watching as the horror of his eyes glistened in the shimmering metal. Twisting the handle in his grasp, Dean made it so the very tip of it dragged down Alastair's pale neck, not breaking any skin along its path though. At last he came to the dip in Alastair's collar bone, just above the point where his sternum would begin. Dean eyed the way the blue-grey fabric of Alastair's dress shirt peeled away at that particular area, revealing nothing but open flesh to him. "No, no," he explained, his voice sounding more hoarse than he would've liked, "Closure's got nothing to do with it. Believe me."

Alastair furrowed his brow in slight confusion – that had certainly not been the answer he was expecting. Still Dean continued on with dragging the knife down his torso, curving and swirling to avoid the buttons of his shirt. "If it's not closure you want, than why could you possibly want to spend so much time with me? Hmm, are you missing me that terribly, Deano??" he pondered as Dean twisted the knife upwards towards his ribs.

Dean simply ignored Alastair's question, feeling he had absolutely nothing to justify to the demon. _Nothing._ As a matter of fact, he really wasn't entirely sure he had the answer figured out himself and so he continued onto a new topic of interest. "You know, if you had a heart, this is where it would be?" Dean murmured quietly, circling the blade in that particular area shredding the fabric ever slightly.

The demon's eyelids fluttered slightly, as this human heart began to pick up speed. Dean was right though – Alastair indeed did not possess a heart, that vaporized some time ago, and so he sort of relied on these stinking corpses to allow him the feelings he couldn't possibly get otherwise. He didn't fully understand why, but there was just something about the mood Dean was in which turned him on like you wouldn't believe. This wasn't the route he expected them to be taking right now, still he played along eager for the boy's next move. Edging his head just slightly off the rack, he moved as close to Dean's ear as he possibly could. "What is it you want, Dean?" Alastair asked, his voice bittersweet with seduction, "There must be something you're prodding at here."

Alastair lifted his stone cold gaze to Dean's – blazing and just full of life. Dean took a moment to debate his answer carefully, pondering just what words would best get his intentions across. "That's a pretty broad question," he began, not wanting to come too close to answering it directly, "There's a lot of things I want Alastair. But you know what I want most of all. Right now?"

"Spill it, I dare you," Alastair muttered in response.

Yet again Dean came so close that it would seem their faces were touching. "I want to hear you scream," Dean declared sadistically, plunging the knife deep into the cavern of bone and flesh. Alastair gritted his teeth, holding off on granting Dean satisfaction for as long as he could. Finally a loud and blood curdling screech echoed from his lips, filling the dull room which surrounded them. Dean beamed widely, bending the blade to his will until he was sure it hit this body's thumping organ – the heart. Chills spread over him as he listened to Alastair shriek, which was like delightful music to his ears. Still, Dean couldn't help but figure that he would get further enjoyment from this if Alastair was screaming _into_ him.

At that thought, Dean tilted his head to the side, covering Alastair's mouth with this own. Slipping their lips together was like beginning to fit a jigsaw puzzle into one masterpiece – everything just seemed to play out so naturally the way they combined. Dean found himself letting go of the knife, leaving it plunged into Alastair, to wrap his hands greedily around the demon's head and pull him closer. Alastair meanwhile, wiggled both his fingers and toes, longing to free so that he could grab at Dean in equal return. His tongue thrashed and swirled against Dean's, as if their make out session were some kind of unspoken competition. He missed Dean – it was undeniable. He missed Dean's filthy stench of lust and self-pride, he missed Dean's accompaniment in meticulous carving of the Hell-bound souls, bust most of all he missed the _taste _of Dean. The hunter's particular flavor of weary sweat, combined with a simply divine tang of lingering alcohol – pure _magic_.

And so, despite his inability to move any of his limbs, Alastair twisted and wriggled forward within Dean's grasp. He gasped loudly as he felt the hunter begin to move downward to his neck, leaving a contradicting trail of soft kisses and rough, tiny bites. Meanwhile, Dean's hands ran rampedly over Alastair's every dip and curve, undoing the buttons of the demon's dress shirt with master precision. Alastair swallowed down a horny lump arising in his throat, wrenching his head upward in desperation as he felt his human member harden below. Unexpectedly, his eyes focused intently on a loose pipe – tiny droplets of water spilt slowly out of its miniscule crack, landing perfectly on the devil's trap. Alastair watched entranced for a moment longer, realizing that he was almost indeed free of these wretched chains. He smiled smugly to himself, understanding that Dean was well oblivious to the situation.

He arched a suspicious eyebrow, watching as Dean was crouched down and working quickly to undo his host's belt buckle. _Ah Dean, always so eager to please, _Alastair mused to himself, _Might as well let you have a little fun before the tables turn._

Dean's hands trembled every slightly as he slipped the belt from its secure position at Alastair's waste, the black khakis now clinging there rather loosely. The hunter barely had to touch them before the fabric flopped down towards the demon's knees. Dean gulped in some kind of nervous frenzy – he felt like a youth again, breaking the rules. The angels had asked him to _torture_ Alastair, not screw him for goodness's sake! Still, he continued with the boxers until at last he caught a glimpse of Alastair's cock ripe and hard. His hazel eyes darted upward for a brief instance, as if asking Alastair for some kind of silent permission. The demon, bearing a most devilish grin, peered back down at him while nodding his head slowly. Dean's tongue swept across his lips delicately, before finally wrapping his entire mouth of Alastair's shaft.

Almost instantly, Alastair nearly purred with satisfaction. Dean could feel his own cock throbbing in anticipation within the confinements of his jeans as he bobbed his head slowly back and forth. There was no real exactness with his sucking, the hunter merely dragging his moist lips down the full length of Alastair, all the way to the tip, before moving forward to envelope the demon as fully as would be allowed. For a while, Alastair clung silently to that rack, his eyes closed and his mouth hanging open as if in a trance. Straining his eyes to simply look up at Alastair once more, Dean could see the demon's Adam's apple bobbing in his throat, along with some major rapid eye movement going on – Alastair was far beyond in enjoy, he was in pure _ecstasy_.

Realizing just how much pleasure Dean was bringing to his old master somehow made the hunter strive to work harder, faster. And then, a strange thought popped into his head – why exactly was he working to please Alastair? After all, it's not like he owed the demon anything or that he was his bitch. No, there was something else – something Dean just couldn't quite put his finger on. Being jerked unexpectedly back to reality, Dean realized that Alastair was indeed thrusting his hips in alignment with Dean's sucking.

Dean's mouth worked strenuously as he could feel pressure beginning to build in the tip of Alastair's cock. He could hear a ragged breathing beginning to echo from Alastair's lips above, knowing that the demon's pulse must be going outrageously fast. Tight waves rippled Alastair's abs as he silently debated to himself how to keep his orgasm best under control – he hadn't experience such bliss in a _very_ long time and so this was indeed a special treat for him. Still, he didn't want Deano getting any ideas thinking that he could just take advantage of him. He continued to pump harder and harder, until his climax could be contained no longer – without warning, Alastair exploded in the confinements of Dean's mouth, splashing thick white release against the walls of Dean's mouth.

Alastair couldn't the extensive delight which surged through him and so he cried out in sheer gratification. To any foreign listener (most likely Castiel, who still stood in the other room), it would appear as though the demon were in deep agony but that couldn't be any further from the truth. Alastair licked his lips, swallowing hard as his mouth had suddenly become very dry.

Dean's mouth, on the other, was anywhere far from dry – almost as soon as Alastair had cum, the young apprentice turned away in disgust, spitting and gagging his master's milk all over the surrounding concrete flooring. Dean stood hunched over, his hands resting firmly on his knees, spewing and coughing as he attempted to rid all of Alastair's release from his mouth. The noises coming from him were simply vile, as though he could vomit any moment. Honestly, it wouldn't surprise Alastair if Dean did.

Feeling as though this quietness had hung between them for far too long, Alastair cleared his throat. "So sorry to have _filled_ you so, my boy," he soothed in content sarcasm.

Dean gritted his teeth bitterly, the demon was much better company when he kept his trap shut. "Screw you," the hunter retorted gruffly. Slowly, Dean stumbled over to the far side of the cart to reach for a bottle of dark colored liquor. Quickly he undid the cap, pressing the glass to his gums – the sweetly invigorating burn washed over his cum-covered tongue, virtually erasing any after taste of Alastair.

The demon chuckled somewhat to himself, murmuring in a low and still seductive tone, "Poor choice of words. I believe I already did there, Deano."

Dean shifted uncomfortably where he stood, thinking back over the scene in his head. Had he really just given a blow job to a demon? Even so, it wasn't so much _that_ thought particularly which appalled him, it was the idea that Alastair believed he'd been in control. People didn't just randomly fuck Dean Winchester's face – no, it simply didn't work that way. Dean was the one doing the fucking here. Period.

Swiftly he turned back to face Alastair, about ready to give him the low-down on how things ran with this whole screwing business, only to find that the demon had somehow managed to overpower the damn devil's trap. "You should talk to your plumber about the pipes," Alastair stated plainly, beaming widely as he planted his fist directly into Dean's face. The hunter went stumbling backwards onto the floor, but Alastair wasn't about to let Dean off that easy. Gripping Dean firmly by throat, Alastair used his super-demon strength to pick him up singlehandedly, bringing them both to eyelevel. He locked their lips in a quick and slimy embrace, before slamming Dean into the rack where he'd been tied up previously. Still holding the hunter firmly, Alastair leaned in close to Dean's ear. "Looks like you're the one back on the rack now," he purred, using Dean's own words against him.

Feeling the demon's hands upon him was almost unbearable to Dean – hot like volcanic ash to the touch. Still, something about this whole situation turned him on oddly enough. Slugging his arms up Alastair's back towards his shoulders, Dean pulled the demon needily closer. Spreading his legs widely, Dean was able to make even more room for Alastair and he to connect, their torsos now touching and rubbing up against one another. Alastair snaked his tongue sneakily into Dean's mouth, sucking on the hunter's bottom lip in the process. Dean moaned softly in return, feeling his once again hard member grinding against Alastair's hips. The demon curled his slender fingers around the side of Dean's torso, grabbing and pulling at the skin in desperation. Repositioning himself more comfortably against his hunter, Alastair wound up knocking Dean roughly into the rack. "Alastair," Dean muttered under his breath, almost in a pleading tone.

Alastair leaned his head close to Dean's shoulder, taking the opportunity to lightly nibble on the boy's ear. He dug his teeth into the soft peach skin of Dean's earlobe, his hands meanwhile working nimbly with Dean's jeans. Without much a hassle, the demon quickly worked them both down to nothing but their boxers, hard cock rubbing against hard cock. For a split second both Dean and Alastair caught each other's gaze, simply pausing – neither one of them dare speak, move, or even breath. Time seemed to stand still, each and every other little important thing slipping away into bleak nothingness.

But then, with a most painful wake to reality, Dean felt Alastair insert himself into him. No lube, no slickness, no nothing – just plain old flesh against flesh. Dean cried out at fist, grasping fistfuls of Alastair's dress shirt within his palms as a sharp pain struck through him. Still as Alastair began to settle into more even pumps and thrusts, Dean felt the tension gradually seeping out of his muscles as pleasure overtook him. Alastair felt a slight grin pulling at his lips, feeling so dominant and in control. He enjoyed the way Dean writhed in blissful agony beneath his weight. The way the hunter cried out his name like he loved him so, and especially the way he clung to the demon in such a needy manner. All these things unquestionably made slipping into one of these costumes all worth the while.

Snaking a hand down in between their heaving bodies, Alastair soon managed to find where Dean's throbbing cock was located and firmly wrapped a hand around it. Immediately, he could feel Dean tense beneath his grasp, but this quickly faded as he began to drag his palm up and down over the shaft. Somehow they pumping matched up with Alastair's strokes into one delightful current. Alastair felt pressure once again beginning to build in his tip, uncertain of how long it typically took Dean to cum. This time, Alastair did little to hold off on his orgasm, releasing hot and thick inside of his hunter. Dean closed his eyes tightly, almost leaning his head on Alastair's shoulder as he felt the white liquid plunge into his depths. Still Alastair continued purposefully on Dean's own cock and soon enough the hunter found himself releasing all over the demon's palm – payback's a bitch.

Alastair paid little mind to his soiled hand, content on rewarding his pet with a slobbery kiss to his plump lips. Both he and Dean panted wildly, feverish with the remnants of their quickly fading orgasms, heaving chest rubbing against one another. Neither one spoke, seeing as words would do little in terms of justification of what was already understood – this was nothing. _Meant_ nothing. Alastair was heartless, thus incapable of loving and Dean could never love a demon. That's just how things were and how they would always stay. This here, was a onetime thing. A one night stand, if you will. Neither Dean or Alastair would be willing or proud to speak to any other about these events and things would just continue with business as usual from here on out.

Still as Alastair laid his head on the hunter's shoulder, and Dean in return, he couldn't help but notice something different had sprouted up inside him. Some unknown spark of electricity which had started lustfully in his member, drifted to his stomach, and now settled contently in the stop in which Dean had stabbed him earlier. Alastair swallowed hard, suddenly unable to stop blinking over his dry eyes. He was Hell's finest torturer, a vicious and ruthless demon created over centuries. He could not love, that emotion was simply an incapability for him. Where a heart should be, only black and cold space lie. Never the less, as he held Dean firmly in his arms, he Alastair desired nothing more than to pull his favorite pupil closer and never let him go. Alastair could not love, but if indeed he could, he would pick a _time_ to describe it rather than a _feeling_. If he had the choice, he would pick Dean Winchester as his lover, and the time to love would be _now._

Alas, no love was to be found between these two partners, and so what was the point of dreaming. Alastair was a demon and could not love – _tristis, tamen verus._

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So I hope this didn't drag on too terribly long, I was just in the mood for romance… what can I say?? Haha ^_^ That last Latin phrase translates to "sad, but true" just to let you know. I'll hopefully be updating on my other works very very soon, so be sure to keep an eye open!

Thanks for reading, **reviews** are undoubtedly appreciated!!


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